Literature DB >> 21202355

Methyl 2-(2-hydroxy-benzyl-ideneamino)-4,5,6,7-tetra-hydro-1-benzothio-phene-3-carboxyl-ate.

Mehmet Akkurt, Selvi Karaca, Abdullah Mohamed Asiri, Orhan Büyükgüngör.   

Abstract

In the title compound, C(17)H(17)NO(3)S, the cyclohexene ring is essentially planar, with a maximum deviation of 0.006 (1) Å. The cyclo-hexene ring adopts a half-chair conformation. The dihedral angle between the thio-phene and benzene rings is 29.7 (1)°. The mol-ecular structure exhibits intra-molecular O-H⋯O, O-H⋯N and C-H⋯S hydrogen bonds, which generate one S(5) and two S(6) motifs. There is also a C-H⋯π inter-action between the cyclo-hexene ring system and the π-system of the benzene ring.

Entities:  

Year:  2008        PMID： 21202355      PMCID： PMC2961328          DOI： 10.1107/S1600536808010489

Source DB:  PubMed          Journal:  Acta Crystallogr Sect E Struct Rep Online        ISSN： 1600-5368


Related literature

For related literature, see: Akkurt et al. (2008 ▶); Allen et al. (1987 ▶); Asiri & Badahdah (2007 ▶); Bernstein et al. (1995 ▶); Cremer & Pople (1975 ▶); Etter (1990 ▶).

Experimental

Crystal data

C17H17NO3S M = 315.39 Monoclinic, a = 7.6107 (4) Å b = 21.2154 (9) Å c = 11.1827 (7) Å β = 123.342 (4)° V = 1508.41 (16) Å3 Z = 4 Mo Kα radiation μ = 0.23 mm−1 T = 293 (2) K 0.60 × 0.47 × 0.23 mm

Data collection

Stoe IPDS2 diffractometer Absorption correction: integration (; Stoe & Cie, 2002 ▶) T min = 0.876, T max = 0.950 8036 measured reflections 3086 independent reflections 2361 reflections with I > 2σ(I) R int = 0.078

Refinement

R[F 2 > 2σ(F 2)] = 0.045 wR(F 2) = 0.121 S = 0.99 3086 reflections 200 parameters H-atom parameters constrained Δρmax = 0.34 e Å−3 Δρmin = −0.41 e Å−3 Data collection: X-AREA (Stoe & Cie, 2002 ▶); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶). Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808010489/is2289sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536808010489/is2289Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C17H17NO3SF000 = 664
Mr = 315.39Dx = 1.389 Mg m−3
Monoclinic, P21/cMo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 10365 reflections
a = 7.6107 (4) Åθ = 1.9–27.2º
b = 21.2154 (9) ŵ = 0.23 mm−1
c = 11.1827 (7) ÅT = 293 (2) K
β = 123.342 (4)ºPlate, yellow
V = 1508.41 (16) Å30.60 × 0.47 × 0.23 mm
Z = 4
Stoe IPDS2 diffractometer3086 independent reflections
Monochromator: plane graphite2361 reflections with I > 2σ(I)
Detector resolution: 6.67 pixels mm-1Rint = 0.078
T = 293(2) Kθmax = 26.5º
ω scansθmin = 1.9º
Absorption correction: integration(X-RED32; Stoe & Cie, 2002)h = −9→9
Tmin = 0.876, Tmax = 0.950k = −23→26
8036 measured reflectionsl = −14→13
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.045  w = 1/[σ2(Fo2) + (0.072P)2] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.121(Δ/σ)max < 0.001
S = 0.99Δρmax = 0.34 e Å−3
3086 reflectionsΔρmin = −0.40 e Å−3
200 parametersExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=KFc[1 + 0.001×Fc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.021 (3)
Secondary atom site location: difference Fourier map
Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles
Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger.
xyzUiso*/Ueq
S10.38087 (8)0.27490 (2)0.37886 (5)0.0508 (2)
O10.7763 (2)0.43178 (7)0.81861 (15)0.0586 (5)
O20.8121 (3)0.28677 (7)0.86144 (15)0.0639 (5)
O30.8298 (3)0.18228 (7)0.85862 (16)0.0662 (5)
N10.6317 (2)0.34975 (7)0.61166 (15)0.0436 (4)
C10.7315 (3)0.45323 (8)0.59125 (18)0.0411 (5)
C20.7924 (3)0.47139 (9)0.7303 (2)0.0450 (5)
C30.8752 (3)0.53085 (10)0.7805 (2)0.0540 (7)
C40.9000 (3)0.57192 (9)0.6957 (3)0.0576 (7)
C50.8421 (3)0.55480 (10)0.5586 (2)0.0577 (7)
C60.7586 (3)0.49630 (9)0.5079 (2)0.0515 (6)
C70.6487 (3)0.39169 (8)0.53568 (19)0.0442 (5)
C80.5536 (3)0.29018 (8)0.55994 (19)0.0425 (5)
C90.6016 (3)0.23555 (8)0.63921 (19)0.0416 (5)
C100.7575 (3)0.23103 (9)0.7957 (2)0.0452 (6)
C110.9685 (4)0.28619 (13)1.0126 (2)0.0705 (8)
C120.4984 (3)0.18131 (8)0.55199 (19)0.0438 (5)
C130.5079 (3)0.11475 (9)0.6026 (2)0.0549 (6)
C140.3347 (3)0.07392 (9)0.4836 (2)0.0572 (7)
C150.3173 (3)0.08294 (10)0.3430 (2)0.0588 (7)
C160.2502 (4)0.14989 (10)0.2891 (2)0.0593 (7)
C170.3767 (3)0.19544 (9)0.41006 (19)0.0457 (6)
H10.725400.398200.777400.0880*
H30.914200.543100.871800.0650*
H40.956400.611700.730600.0690*
H50.859800.582800.502000.0690*
H60.719100.484900.416000.0620*
H70.606300.381900.442400.0530*
H11A1.096300.268201.029900.0850*
H11B0.919000.261401.060200.0850*
H11C0.994700.328501.048700.0850*
H13A0.493000.115300.683300.0660*
H13B0.643900.096600.634600.0660*
H14A0.364000.030000.511500.0690*
H14B0.201300.084500.470700.0690*
H15A0.215200.053500.272600.0700*
H15B0.452200.074300.356300.0700*
H16A0.272100.158300.212900.0710*
H16B0.101700.155100.250900.0710*
U11U22U33U12U13U23
S10.0565 (3)0.0466 (3)0.0366 (3)−0.0026 (2)0.0176 (2)0.0017 (2)
O10.0796 (9)0.0573 (8)0.0470 (8)−0.0121 (7)0.0400 (7)−0.0047 (7)
O20.0802 (10)0.0530 (8)0.0349 (7)−0.0107 (7)0.0166 (7)0.0015 (6)
O30.0735 (9)0.0563 (9)0.0482 (8)0.0110 (7)0.0204 (7)0.0089 (7)
N10.0454 (7)0.0411 (8)0.0389 (8)0.0005 (6)0.0197 (6)0.0023 (6)
C10.0400 (8)0.0424 (9)0.0416 (9)0.0054 (7)0.0228 (7)0.0039 (7)
C20.0482 (9)0.0446 (9)0.0475 (10)0.0020 (7)0.0297 (8)0.0005 (8)
C30.0593 (11)0.0515 (11)0.0558 (12)−0.0004 (9)0.0345 (10)−0.0085 (9)
C40.0577 (11)0.0404 (10)0.0765 (15)−0.0011 (8)0.0381 (11)−0.0031 (10)
C50.0647 (12)0.0488 (11)0.0647 (13)0.0010 (9)0.0388 (11)0.0115 (10)
C60.0574 (10)0.0532 (11)0.0470 (10)0.0011 (9)0.0306 (9)0.0049 (9)
C70.0461 (9)0.0475 (10)0.0373 (9)0.0035 (7)0.0219 (7)0.0011 (8)
C80.0427 (8)0.0432 (9)0.0385 (9)0.0007 (7)0.0204 (7)−0.0008 (8)
C90.0423 (8)0.0429 (9)0.0384 (9)0.0001 (7)0.0215 (7)0.0026 (7)
C100.0448 (9)0.0482 (10)0.0414 (10)−0.0014 (7)0.0230 (8)0.0022 (8)
C110.0794 (15)0.0785 (15)0.0361 (10)−0.0213 (12)0.0207 (10)−0.0009 (10)
C120.0417 (8)0.0435 (9)0.0443 (9)−0.0005 (7)0.0225 (8)0.0007 (8)
C130.0586 (11)0.0464 (10)0.0527 (11)−0.0021 (8)0.0262 (9)0.0054 (9)
C140.0635 (11)0.0457 (10)0.0665 (13)−0.0071 (9)0.0384 (11)−0.0037 (10)
C150.0636 (11)0.0529 (11)0.0619 (13)−0.0089 (9)0.0358 (10)−0.0117 (10)
C160.0657 (12)0.0575 (12)0.0460 (11)−0.0116 (9)0.0251 (10)−0.0100 (9)
C170.0474 (9)0.0446 (10)0.0423 (10)−0.0034 (7)0.0229 (8)−0.0017 (8)
S1—C81.7342 (18)C13—C141.527 (3)
S1—C171.725 (2)C14—C151.516 (3)
O1—C21.353 (3)C15—C161.518 (3)
O2—C101.333 (2)C16—C171.503 (3)
O2—C111.436 (2)C3—H30.9300
O3—C101.201 (2)C4—H40.9300
O1—H10.8200C5—H50.9300
N1—C81.381 (2)C6—H60.9300
N1—C71.285 (2)C7—H70.9300
C1—C21.410 (3)C11—H11A0.9600
C1—C71.434 (2)C11—H11B0.9600
C1—C61.399 (3)C11—H11C0.9600
C2—C31.384 (3)C13—H13A0.9700
C3—C41.375 (3)C13—H13B0.9700
C4—C51.391 (3)C14—H14A0.9700
C5—C61.367 (3)C14—H14B0.9700
C8—C91.381 (2)C15—H15A0.9700
C9—C101.482 (3)C15—H15B0.9700
C9—C121.432 (2)C16—H16A0.9700
C12—C171.361 (3)C16—H16B0.9700
C12—C131.508 (3)
S1···C11i3.543 (2)C7···H16Bv3.0900
S1···C10ii3.468 (3)C8···H11Bii2.9900
S1···H72.6900C8···H13.0600
O1···O23.102 (2)C9···H11Bii2.9900
O1···N12.607 (2)C10···H13A2.9800
O2···N12.694 (2)C12···H15B3.0400
O2···O13.102 (2)C17···H14B2.9600
O3···C4iii3.384 (3)H1···O22.5000
O3···C7iv3.359 (3)H1···N11.8800
O3···C132.923 (3)H1···C72.4400
O1···H15Biv2.7200H1···C83.0600
O1···H14Bv2.7300H3···H14Bix2.5200
O2···H12.5000H4···O3vii2.7700
O3···H13A2.6300H4···H13Bvii2.5700
O3···H13B2.7700H5···O3vii2.9000
O3···H11B2.5800H5···H16Ax2.5900
O3···H4iii2.7700H6···H72.4200
O3···H5iii2.9000H7···S12.6900
O3···H11A2.6100H7···H62.4200
O3···H7iv2.7200H7···O3ii2.7200
N1···O12.607 (2)H7···H13Aii2.5300
N1···O22.694 (2)H11A···O32.6100
N1···H11.8800H11B···O32.5800
C1···C1vi3.552 (3)H11B···C8iv2.9900
C1···C6vi3.427 (3)H11B···C9iv2.9900
C2···C6vi3.588 (3)H13A···O32.6300
C4···C7vi3.585 (4)H13A···C102.9800
C4···O3vii3.384 (3)H13A···H7iv2.5300
C5···C7vi3.468 (4)H13B···O32.7700
C6···C2vi3.588 (3)H13B···C4iii2.9500
C6···C1vi3.427 (3)H13B···H4iii2.5700
C7···O3ii3.359 (3)H14A···H14Axi2.5600
C7···C5vi3.468 (4)H14B···C172.9600
C7···C4vi3.585 (4)H14B···H3xii2.5200
C10···S1iv3.468 (3)H14B···O1xiii2.7300
C11···S1viii3.543 (2)H14B···C2xiii3.0200
C13···O32.923 (3)H15A···C1xiii3.0800
C1···H15Av3.0800H15A···C2xiii3.0300
C2···H15Av3.0300H15B···C123.0400
C2···H14Bv3.0200H15B···O1ii2.7200
C4···H13Bvii2.9500H16A···H5xiv2.5900
C7···H12.4400H16B···C7xiii3.0900
C8—S1—C1791.89 (9)C4—C3—H3120.00
C10—O2—C11116.56 (17)C3—C4—H4119.00
C2—O1—H1109.00C5—C4—H4120.00
C7—N1—C8122.23 (16)C4—C5—H5120.00
C2—C1—C7121.75 (18)C6—C5—H5120.00
C6—C1—C7119.76 (17)C1—C6—H6119.00
C2—C1—C6118.47 (17)C5—C6—H6119.00
O1—C2—C1121.91 (17)N1—C7—H7119.00
O1—C2—C3118.30 (17)C1—C7—H7119.00
C1—C2—C3119.79 (19)O2—C11—H11A109.00
C2—C3—C4120.16 (19)O2—C11—H11B109.00
C3—C4—C5121.0 (2)O2—C11—H11C109.00
C4—C5—C6119.2 (2)H11A—C11—H11B109.00
C1—C6—C5121.44 (18)H11A—C11—H11C110.00
N1—C7—C1121.58 (17)H11B—C11—H11C109.00
S1—C8—N1122.39 (13)C12—C13—H13A109.00
N1—C8—C9126.74 (16)C12—C13—H13B109.00
S1—C8—C9110.86 (13)C14—C13—H13A109.00
C8—C9—C10124.74 (17)C14—C13—H13B109.00
C10—C9—C12122.39 (16)H13A—C13—H13B108.00
C8—C9—C12112.63 (16)C13—C14—H14A109.00
O2—C10—C9113.48 (16)C13—C14—H14B109.00
O3—C10—C9124.00 (17)C15—C14—H14A109.00
O2—C10—O3122.52 (18)C15—C14—H14B109.00
C9—C12—C17112.61 (16)H14A—C14—H14B108.00
C13—C12—C17120.37 (16)C14—C15—H15A110.00
C9—C12—C13126.99 (16)C14—C15—H15B110.00
C12—C13—C14111.34 (16)C16—C15—H15A110.00
C13—C14—C15111.96 (19)C16—C15—H15B110.00
C14—C15—C16110.40 (18)H15A—C15—H15B108.00
C15—C16—C17109.58 (16)C15—C16—H16A110.00
S1—C17—C16121.34 (14)C15—C16—H16B110.00
C12—C17—C16126.65 (17)C17—C16—H16A110.00
S1—C17—C12112.01 (14)C17—C16—H16B110.00
C2—C3—H3120.00H16A—C16—H16B108.00
C17—S1—C8—C9−0.8 (2)N1—C8—C9—C10−3.6 (4)
C17—S1—C8—N1177.8 (2)S1—C8—C9—C10174.9 (2)
C8—S1—C17—C121.0 (2)N1—C8—C9—C12−178.1 (2)
C8—S1—C17—C16−178.8 (2)C8—C9—C12—C13−177.4 (2)
C11—O2—C10—C9−177.8 (2)C8—C9—C12—C170.4 (3)
C11—O2—C10—O31.9 (4)C12—C9—C10—O310.0 (4)
C7—N1—C8—C9152.2 (3)C8—C9—C10—O215.7 (4)
C7—N1—C8—S1−26.2 (3)C8—C9—C10—O3−164.0 (3)
C8—N1—C7—C1−179.6 (2)C12—C9—C10—O2−170.3 (2)
C2—C1—C6—C50.1 (4)C10—C9—C12—C137.9 (4)
C7—C1—C2—O10.1 (4)C10—C9—C12—C17−174.3 (2)
C6—C1—C7—N1176.4 (2)C9—C12—C13—C14164.9 (2)
C7—C1—C2—C3178.8 (2)C9—C12—C17—C16178.9 (3)
C2—C1—C7—N1−1.9 (4)C17—C12—C13—C14−12.7 (3)
C6—C1—C2—O1−178.2 (2)C9—C12—C17—S1−1.0 (3)
C7—C1—C6—C5−178.3 (2)C13—C12—C17—C16−3.2 (4)
C6—C1—C2—C30.5 (4)C13—C12—C17—S1177.03 (19)
C1—C2—C3—C4−0.6 (4)C12—C13—C14—C1545.8 (3)
O1—C2—C3—C4178.1 (2)C13—C14—C15—C16−64.5 (3)
C2—C3—C4—C50.3 (4)C14—C15—C16—C1745.7 (3)
C3—C4—C5—C60.3 (4)C15—C16—C17—C12−13.8 (4)
C4—C5—C6—C1−0.4 (4)C15—C16—C17—S1166.03 (19)
S1—C8—C9—C120.4 (3)
D—H···AD—HH···AD···AD—H···A
O1—H1···O20.822.503.102 (2)132
O1—H1···N10.821.882.607 (2)146
C7—H7···S10.932.693.0725 (19)105
C15—H15A···Cgxiii0.972.923.782 (3)150
Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯AD—HH⋯AD⋯AD—H⋯A
O1—H1⋯O20.822.503.102 (2)132
O1—H1⋯N10.821.882.607 (2)146
C7—H7⋯S10.932.693.0725 (19)105
C15—H15A⋯Cgi0.972.923.782 (3)150

Symmetry code: (i) . Cg is the centroid of the benzene ring.

  3 in total

1.  A short history of SHELX.

Authors:  George M Sheldrick
Journal:  Acta Crystallogr A       Date:  2007-12-21       Impact factor: 2.290

2.  Synthesis of some new anils: part 1. Reaction of 2-hydroxy-benzaldehyde and 2-hydroxynaphthaldehyde with 2-aminopyridene and 2-aminopyrazine.

Authors:  Abdullah M Asiri; Khadija O Badahdah
Journal:  Molecules       Date:  2007-08-13       Impact factor: 4.411

3.  4-[(2-Hydr-oxy-1-naphth-yl)methyl-idene-amino]benzoic acid.

Authors:  Mehmet Akkurt; Sema Öztürk Yıldırım; Abdullah Mohamed Asiri; Vickie McKee
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2008-03-07
  3 in total
  5 in total

1.  Diethyl 5-[(2-hydr-oxy-1-naphth-yl)methyl-ideneamino]-3-methyl-thio-phene-2,4-dicarboxyl-ate.

Authors:  Mehmet Akkurt; Serife Pınar Yalçın; Abdullah Mohamed Asiri; Orhan Büyükgüngör
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2008-04-26

2.  2-Amino-7-oxo-4,5,6,7-tetra-hydro-1-benzothio-phene-3-carbonitrile.

Authors:  Mohamed Ziaulla; Afshan Banu; Noor Shahina Begum; Shridhar I Panchamukhi; I M Khazi
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2010-09-25

3.  2-Phenyl-8,9,10,11-tetra-hydro-1-benzo-thieno[3,2-e][1,2,4]triazolo[1,5-c]pyrimidine.

Authors:  Shridhar I Panchamukhi; Nikhath Fathima; I M Khazi; Noor Shahina Begum
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2011-03-05

4.  2-Amino-6-methyl-4,5,6,7-tetra-hydro-1-benzothio-phene-3-carbonitrile.

Authors:  Mohamed Ziaulla; Afshan Banu; Noor Shahina Begum; Shridhar I Panchamukhi; I M Khazi
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2011-02-23

5.  7-Methyl-5,6,7,8-tetra-hydro-1-benzo-thieno[2,3-d]pyrimidin-4-amine.

Authors:  Mohamed Ziaulla; Afshan Banu; Noor Shahina Begum; Shridhar I Panchamukhi; I M Khazi
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2011-06-11
  5 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.